Benzyl Bromide → HCID 15442177, compound

HRID 2262727Notes

Reaction equation

HRID 2262727 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=[O:10].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:24]([N:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:9]([CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]1)=[O:10])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 15442175HCID 15442175, compound

Product 1

HCID 15442177HCID 15442177, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 4-[(2-bromophenyl)carbamoyl]piperidine-1-carboxylate (8 mmol), benzylbromide (1.05 ml, 8.8 mmol) and Cs2CO3 (5.2 g, 16 mmol) in DMF (20 ml) is stirred at rt overnight. DMF is removed in vacuo and the residue is partitioned between H2O (40 ml) and EtOAc (40 ml). The layers are separated and the aqueous layer is extracted with EtOAc (20 ml). The combined extracts are washed with brine (20 ml), dried over Na2SO4 and evaporated. The residue is purified by flash column to give the title compound as a light yellow oil.

Workup

  1. customDMF is removed in vacuo
  2. customthe residue is partitioned between H2O (40 ml) and EtOAc (40 ml)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (20 ml)
  5. washThe combined extracts are washed with brine (20 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue is purified by flash column

Sources & evidence

ORD record
ord-1d677c01067c45c9b1cae1ce525951ef
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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